Methanol → Methyl 3-[2-(2,6-dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolecarboxylate

Participants

Reaction Steps

A solution of methyl isobutyrylacetate (0.662 g, 5.8 mmol) in tetrahydrofuran (1.16 mL) was stirred at 0° C. as 0.5 N sodium methoxide in methanol solution (11.6 mL, 5.8 mmol) was added. A solution of 3-(2,6-dichlorophenyl)-N-hydroxypropanimidoyl chloride (1.04 g, 4.82 mmol) in tetrahydrofuran (3.8 mL) was added and the solution was allowed to warm to room temperature and was stirred overnight. The mixture was concentrated and the residue triturated with water and filtered to yield a white solid which was dried in a 45° C. oven with P2O5 under reduced pressure to yield the title compound (0.926 g, 56%). 1H NMR (DMSO-d6): 7.43 (d, J=8 Hz, 2H), 7.25 (t, J=8 Hz, 1H), 3.73 (s, 3H), 3.67 (septet, J=7 Hz, 1H), 3.24-3.20 (m, 2H), 3.07-3.03 (m, 2H), 1.23 (d, J=7 Hz, 6H).

Provenance & Evidence